HCID 67581870, compound → HCID 57011354, compound

HRID 1416479Notes

Reaction equation

HRID 1416479 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][C@@H:28]3[CH2:32][C@H:31]([O:33][CH3:34])[C@@H:30]([OH:35])[C@H:29]3[OH:36])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[OH:36][C@@H:29]1[C@H:30]([OH:35])[C@@H:31]([O:33][CH3:34])[CH2:32][C@H:28]1[O:27][C:25]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([N:14]2[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]2)[N:26]=1

Participants

4

Reactant 1

HCID 67581870HCID 67581870, compound

Product 1

HCID 57011354HCID 57011354, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(1R,2R,3S,4S)-(2,3-dihydroxy-4-methoxycyclopentan-1-yl)oxy]quinazoline (5.40 g) in methanol (108 ml) is added 10% palladium/carbon (1.00 g), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 16.5 hours. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure, and the residue is crystallized from diethyl ether to give 4-[(1R,2R,3S,4S)-(2,3-dihydroxy-4-methoxycyclopentan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (2.95 g) as crystals. A part of this product is recrystallized from ethanol-diethyl ether to give a pure crystalline product, which has the following physical properties.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness under reduced pressure
  3. customthe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-b77b0e29b42c41ff9c75ea34f2dfdf80
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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